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Red Ruffing was a Hall of Fame pitcher who spent most of his career with the New York Yankees. He never had a winning season in his first six seasons with the Boston Red Sox, who were a terrible team, but he was a big winner with the Yankees.

He originally played outfield but switched to pitching after losing four toes as a teenager in a mining accident. With the New York Yankees, he was the winning pitcher in seven World Series games (for a 7-2 lifetime mark) and was a twenty game winner in four consecutive seasons. He was also known as a very good hitting pitcher, smashing 36 homers in his career.

The 37-year-old Ruffing was inducted into the Air Force in December 1942 and was discharged in June 1945.

Ruffing quote: "I always figured World Series games the easiest to pitch. The other team didn't know you...and on the Yankees, we used to figure the National League champion only good enough to finish third or fourth in the American League."

He made the Hall of Fame despite an extremely rocky start to his career. Among all Hall of Famer pitchers we have the proper info for* and who lost at least 100 games, here were their Won-Loss records at the time of their 100th loss (please note how far back Ruffing is from even next-to-last):

1. 232-100 Whitey Ford

2. 228-100 Lefty Grove

3. 206-100 Juan Marichal

4. 185-100 Lefty Gomez

5. 184-100 Carl Hubbell

6. 182-100 Jim Palmer

7. 178-100 Bob Feller

8. 176-100 Bob Lemon

9. 173-100 Tom Seaver

10. 159-100 Robin Roberts

11. 155-100 Waite Hoyt

12t. 154-100 Dazzy Vance

12t. 154-100 Stan Coveleski

14. 153-100 Bob Gibson

15. 151-100 Red Faber

16. 148-100 Warren Spahn

17. 144-100 Fergie Jenkins

18. 142-100 Jim Bunning

19. 136-100 Don Drysdale

20. 133-100 Catfish Hunter

21. 132-100 Hal Newhouser

22. 131-100 Steve Carlton

23. 128-100 Herb Pennock

24t. 124-100 Gaylord Perry

24t. 124-100 Burleigh Grimes

26. 123-100 Ted Lyons

27. 120-100 Dennis Eckersley

28. 118-100 Jesse Haines

29. 118-100 Phil Niekro

30. 117-100 Rich Gossage

31. 116-100 Hoyt Wilhelm

32. 114-100 Don Sutton

33. 108-100 Nolan Ryan

34. 99-100 Rollie Fingers

35. 98-100 Early Wynn

36. 86-100 Eppa Rixey

37. 53-100 Red Ruffing

This means those who lost their 100th game from 1920-onward, when reliable game logs are easily accessible.